rac-(3R,5S)-{5-[(E)-2-({4'-Chloro-4-fluoro-[1,1'-biphenyl]-2-yl}methylidene)hydrazin-1-yl]piperidine-3-carboxylic acid}

ID: ALA4447559

PubChem CID: 155518880

Max Phase: Preclinical

Molecular Formula: C19H19ClFN3O2

Molecular Weight: 375.83

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(O)[C@H]1CNC[C@@H](N/N=C/c2cc(F)ccc2-c2ccc(Cl)cc2)C1

Standard InChI:  InChI=1S/C19H19ClFN3O2/c20-15-3-1-12(2-4-15)18-6-5-16(21)7-13(18)10-23-24-17-8-14(19(25)26)9-22-11-17/h1-7,10,14,17,22,24H,8-9,11H2,(H,25,26)/b23-10+/t14-,17+/m1/s1

Standard InChI Key:  MATCLQIZQUZJIL-GOUPHMKNSA-N

Molfile:  

 
     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
    7.5148   -9.6982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8004  -10.1152    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0836   -9.7025    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3692  -10.1194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6525   -9.7066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6543   -8.8820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9383   -8.4734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2229   -8.8863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2280   -9.7161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9445  -10.1252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9511  -10.9479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2371  -11.3635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2430  -12.1883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9623  -12.5985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6770  -12.1737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6676  -11.3503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9697  -13.4242    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.9363   -7.6478    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    8.2247  -10.1130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9370   -9.6995    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.9389   -8.8735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2222   -8.4628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5079   -8.8737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2226   -7.6370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9383   -7.2225    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5114   -7.2219    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  1
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10  5  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 11  1  0
 10 11  1  0
 14 17  1  0
  7 18  1  0
  1 19  1  0
  1 23  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  1  1
 24 25  2  0
 24 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4447559

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 375.83

Molecular Weight (Monoisotopic): 375.1150

AlogP: 3.13

#Rotatable Bonds: 5

Polar Surface Area: 73.72

Molecular Species: ZWITTERION

HBA: 4

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.33

CX Basic pKa: 8.99

CX LogP: 1.03

CX LogD: 1.02

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.55

Np Likeness Score: -0.81

References

1. Hauke TJ, Höfner G, Wanner KT..  (2019)  Generation and screening of pseudostatic hydrazone libraries derived from 5-substituted nipecotic acid derivatives at the GABA transporter mGAT4.,  27  (1): [PMID:30503411] [10.1016/j.bmc.2018.11.028]

Source

Source(1):

• Scientific Literature